But Tribune Co. employees are unlikely to see any gain from their brief stint as owners of their company through a transaction engineered by Zell that left the Chicago media firm saddled with $13 billion in debt, bankruptcy experts said.

Tribune Co., after United Airlines, is the second major Chicago company to seek bankruptcy protection this decade after forming an employee stock ownership plan.

In engineering a deal to take the media company private last year, Zell struck an agreement that left him poised to benefit richly if the complex transaction succeeded, while potentially hedging his losses if Tribune Co. wound up in bankruptcy.

For $315 million, entities affiliated with Zell bought a $225 million "subordinated promissory note" as well as warrants that would allow Zell to eventually buy 40 percent of Tribune Co. for as little as $500 million.

"He's a very smart guy and structured this to benefit him all the way," said Chicago compensation expert Don Delves.

The $225 million note means that Zell-controlled entities are a major unsecured creditor and, under bankruptcy law, will be compensated ahead of shareholders when a Delaware bankruptcy judge settles Tribune Co.'s debts, Monday's bankruptcy filings indicate.

Experts think the leveraged ESOP that gave Tribune Co. employees theoretical control of their company will likely be wiped out.

"The ESOP still exists and its value and role, long term, will be determined in the restructuring," said Gary Weitman, a spokesman for Tribune Co., which owns the Chicago Tribune and other media properties.

While United workers funded their ESOP by deferring pay raises, Tribune Co. workers stood to gain stock as their company paid off debt. Tribune Co. workers aren't vested yet, and the plan, less than 2 years old, hasn't garnered significant assets.

"Employees are marginally worse off now than before the ESOP," said Corey Rosen, executive director of the National Center for Employee Ownership.

For now, Tribune Co. says it intends to continue paying pensions, which aren't part of the ESOP.

Tribune Co. paid $59.5 million from pension assets as special one-time pension payments to 1,500 employees who left the company during the first nine months of this year. The company said Monday that it had stopped ongoing severance and deferred-compensation payments to a handful of former employees, who will be required to file a claim with the court.

The bankruptcy filing comes less than three months after a group of six current and former Los Angeles Times employees sued Zell and Tribune Co. over the deal. The suit states: "Because Zell's outlay is primarily debt, Zell has greater protection in the event of bankruptcy; the employee-owners' shares, as equity, would not."

Phil Gregory, an attorney representing those suing Zell, said Monday: "This is exactly what we said would happen."